97. Madonna

It's not often that one can profess to have had flings with two different baseball eras' faces of steroid abuse. However, Madonna has always been an innovator, and in WAGdom, she is no different. Madonna followed up a reported 1991 tryst with Jose Canseco by allegedly hooking up with Alex Rodriguez in 2008. As if this series of partners were not bizarre enough, she somehow found the time to date notorious psychopath and prolific NBA rebounder Dennis Rodman in 1996. If there was any question remaining as to Madonna's sanity level, Rodman has openly stated that she "wanted to have my babies."